3-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole → 3-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-indole

HRID 893327Notes

Reaction equation

HRID 893327 reaction equation
[CH2:1]1[O:19][C:4]2([CH2:9][CH2:8][C:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)=[CH:6][CH2:5]2)[O:3][CH2:2]1.[H][H]>O1CCCC1.CO.[Pd]>[CH2:2]1[O:3][C:4]2([CH2:9][CH2:8][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:19][CH2:1]1

Participants

6

Reactant 2

HCID 27638573-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 108487533-(1,4-dioxaspiro[4.5]decan-8-yl)-1H-indoleYield 100,141.703%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(1H-3-indolyl)-3-cyclohexenone ethylene ketal (66.6 g, 0.26 mmol) is dissolved in 500 mL of tetrahydrofuran and 100 mL of methanol, 1.0 g 5% palladium on carbon is added and the mixture is placed under 60 pounds per square inch (psi) of hydrogen. After 2 hours the reaction is filtered and concentrated to give the product as a tan solid (67.0 g). An analytical sample is recrystallized from methanol; mp 163°-5° C.

Workup

  1. filtrationAfter 2 hours the reaction is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5095abcc2d1540e8afd81f5764d58fd8
Source dataset
uspto-grants-1992_06
Patent number
US05124332

Reaction notes

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